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Process for the preparation of the sodium salt of 6[D-(-)alpha-4-(ethyl-2,3-dioxo-1-piperazinocarbonylamino) phenylacetamido]penicillanic acid

a technology of phenylacetamido and process, which is applied in the field of process for the preparation of the sodium salt of 6d() alpha4(ethyl2, 3dioxo1piperazinocarbonylamino) phenylacetamidoopenicillanic acid, can solve the problems of considerable drawbacks of processes when scaled up to industrial level

Inactive Publication Date: 2003-02-06
IST BIOCHIM ITALANO GIOVANNI LORENZINI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such processes, when scaled up to industrial level, show considerable drawbacks, especially when they are meant for the production of a sterile sodium salt.

Method used

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Examples

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Effect test

example 2

[0041] Preparation of the Sodium Salt of 6[D-(-).alpha.-4-(ethyl-2.3-dioxo--1-piperazinocarbonylamino)Phenyl Acetamido]Penicillanic Acid

[0042] The three following solutions were prepared:

[0043] SOLUTION A) prepared as per Example 1

[0044] SOLUTION B) prepared as per Example 1

[0045] SOLUTION C) 420 ml of acetone, 18 ml of methyl isobutyl ketone and 2.8 ml of water were mixed.

[0046] The method of Example 1 was followed to give 55.1 g of 6[D-(-).alpha.-4-(ethyl-2,3-dioxo-1-piperazinocarbonylamino)phenylacetami-do]penicillanic acid in the form of sodium salt monohydrate (sodium salt content by HPLC 96.74% (anhydrous basis), water quantity, calculated by Karl Fisher's method, 3.3%).

example 3

[0047] Preparation of the Sodium Salt of 6[D-(-).alpha.-4-(ethyl-2.3-dioxo--1-piperazinocarbonylamino)Phenyl Acetamido]Penicillanic Acid

[0048] The two following solutions were prepared:

[0049] SOLUTION A) 120 g of 6[D-(-).alpha.-4-(ethyl-2,3-dioxo-1-piperazino-carbonylamino) phenylacetamido]penicillanic acid was dissolved in 250 ml of acetone; 31.6 ml of triethylamine was added during 5 min with vigorous stirring, which was continued until complete dissolution.

[0050] SOLUTION B) 39.6 g of sodium 2-ethyl hexanoate was dissolved in 1,000 ml of acetone at 15.degree. C.

[0051] SOLUTION A) was thread-poured into SOLUTION B) with vigorous stirring at a temperature of 150 to 18.degree. C. Once the addition was completed, the rate of stirring was reduced to 20-30 rpm, while the temperature was maintained at 15.degree. to 18.degree. C. for 90 min.

[0052] The resulting product was recovered by filtration, washed and suspended again twice with 500 ml of acetone. The product was oven dried under v...

example 4

[0053] Preparation of the Sodium Salt of 6[D-(-).alpha.-4-(ethyl-2.3-dioxo--1-piperazinocarbonylamino)Phenyl Acetamido]Penicillanic Acid

[0054] A 1 l flask was fed with 182.5 ml of isopropyl alcohol, 182.5 ml of acetonitrile and 182.5 ml of acetone. 100 g of 6[D-(-).alpha.-4-(ethyl-2,-3-dioxo-1-piperazinocarbonylamino)phenyl acetamido]penicillanic acid was added portionwise under vigorous stirring. Stirring was continued for approx. 15 min until complete solubilisation. The solution was then added with 8.3 ml of water and allowed to stir for additional 5 min.

[0055] 33.2 g of sodium 2-ethyl hexanoate was added portionwise over 15 to 20 min. The solution was allowed to stir for approx. 30 min until complete solubilisation. The resulting solution was fed, over approx. 15 min and with vigorous stirring, to a 3 l flask containing 1,825 ml acetone.

[0056] The 1 l flask that had contained the solution was washed with a mixture consisting of 3.6 ml of acetone, 3.6 ml of acetonitrile and 3.6 m...

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Abstract

The present invention refers to the preparation process of the sodium salt of 6[D-(-)alpha-4-(ethyl-2,3-dioxo-1-piperazinocarbonylamino) phenylacetamido]penicillanic acid, comprising the reaction of the acid with a reagent selected from the group consisting of sodium hydroxide, sodium carboxylates and sodium alcoholates, followed by a separation step of the so obtained sodium salt by precipitation.

Description

[0001] The present invention refers to a preparation process of the sodium salt of 6[D-(-).alpha.-4-(ethyl-2,3-dioxo-1-piperazinocarbonylamino)pheny-lacetamido]penicillanic acid, useful as active ingredient in the treatment of pneumonia, peritonitis and blood infection.STATE OF THE ART[0002] Many preparation processes of the sodium salt of penicillanic acids and, in particular of 6[D-(-).alpha.-4-(ethyl-2,3-dioxo-1-piperazinocarbo-nylamino) phenylacetamido]penicillanic acid are already known.[0003] By way of example, mention is made of the processes described in the European Patent Application No. EP 294 789 or in the US Patent No. U.S. Pat. No. 4,112,090. Such processes, when scaled up to industrial level, show considerable drawbacks, especially when they are meant for the production of a sterile sodium salt. For example, when the salification is carried out with sodium 2-ethyl hexanoate, the sodium salt content, determined in the salification product by HPLC, is low because of the...

Claims

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Application Information

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IPC IPC(8): C07D499/00C07D499/14C07D499/16C07D499/68C07D499/76
CPCC07D499/00
Inventor BRANDT, ALBERTOCECCHETELLI, LOREDANACORSI, GIORDANO BRUNOSIMEONI, ANTONIO
Owner IST BIOCHIM ITALANO GIOVANNI LORENZINI
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